Critical design has been philosophically positioned as that which opposes the affirmative role of design as the status quo, offering itself as social critique located in the formalised spaces of museums and galleries. This paper contests that reasoning by firstly showing that in the contemporary sphere, criticality in design now resides in a more socially aware and humanistically engaged space. Design propositions can be expressed from the perspective of modes of enquiry that ask both What if? and How else? questions in the vein of Malpass and Slotnick. These then propose alternative ways of considering design not as a way of seeking answers but as a way of asking questions.